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The group was formed around the nucleus of childhood friends Jeff Barry and Ellie Greenwich. Greenwich had recorded a single in 1958 ("Cha-Cha Charming", as by Ellie Gaye) while a college student, and Barry began working for a Brill Building music publisher in 1959, penning the hit "Tell Laura I Love Her" amongst others. The two met again that year and began dating; simultaneously, they began writing songs together, mainly for other artists. However, a couple of Greenwich-led discs were issued in the early 1960s under pseudonyms, one credited to Ellie Gee and The Jets, another to Kelli Douglas.

Greenwich and Barry would marry in October 1962. Greenwich also got a job in music publishing, not only writing but also singing on various demos of her publisher's songs.

In early 1963, Greenwich and Barry recorded a demo of their composition "What a Guy", a tune Barry had written for The Sensations. However, the group's label, Jubilee Records, chose to release Barry and Greenwich's demo as the single under the name 'The Raindrops' (the group name was reportedly inspired by "Raindrops," a 1961 hit song by Dee Clark).

The single hit #41 on the U.S.Billboard Hot 100, and the follow-up, "The Kind of Boy You Can't Forget", hit #17. The Raindrops sound was "girl-group" in style, with Greenwich singing lead vocal and double-tracked harmony parts, and Barry providing nonsense-syllable bass vocals.

At this point, the group began to attract attention. Media stills of the group often depicted the group as a trio, featuring Greenwich and Barry as well as Greenwich's younger sister Laura, who did not sing on the records. The Raindrops made occasional live appearances, but rarely with the same personnel as on record; Ellie Greenwich sometimes had Beverly Warren sing live for her, and Bobby Bosco filled in at times for Barry. To preserve the illusion that the group was a trio, Laura Greenwich also occasionally appeared in live performances with the group, singing into a dead microphone.

The Raindrops released an album on Jubilee towards the end of 1963; a third single, "That Boy John", was a minor hit but sank at radio after the assassination of John F. Kennedy. After a few further minor hits, Barry and Greenwich stopped releasing material as The Raindrops in early 1965, around the same time they became involved with Red Bird Records.

Both Greenwich and Barry enjoyed successful careers as songwriters after the demise of The Raindrops, and Greenwich went on to a modest solo career as a singer as well. They divorced late in 1965, although they continued to write songs together for a time. They reunited on record for a 1967 single credited to The Meantime, which failed to chart. This was their last professional project as a duo.